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Enterprise Sales Tactics for PLG Success

Strategy
June 28, 2025
Kim Graves shares winning sales strategies from Notion and Slack, including PLG layering, hiring grit, and AI resistance.
Topics discussed in the episode:
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How do PLG companies successfully incorporate enterprise sales without conflict?
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How should founders handle compensation negotiations with new sales hires?
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What are key considerations when onboarding new sales reps?
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How can startups improve their sales process by focusing on mindset?
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How can startups leverage AI to enhance their sales efforts?
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How can startups prevent deals from stalling due to single-threading?
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Why is cold calling still effective in sales?
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When should startups start outbound sales efforts?
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What type of sales reps should startups hire first?
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How should founders define their ideal customer profile (ICP) in a PLG startup?

How do PLG companies successfully incorporate enterprise sales without conflict?

Incorporating enterprise sales into a PLG company requires alignment and education.

\"...The best companies I've seen layer sales on top of product led growth.\"

Takeaway:
  • Recognize that sales and PLG can coexist and complement each other.
  • Ensure alignment between sales teams and product initiatives.
  • Educate the organization on the value of sales in driving growth.

How should founders handle compensation negotiations with new sales hires?

Compensation discussions with sales hires require transparency and alignment with company stage.

\"The expectations are set upfront... If you're just looking to maximize your OTE that's probably not the best place... You also want to think about the equity and the full package.\"

Takeaway:
  • Set clear compensation expectations early in the hiring process.
  • Emphasize the importance of equity and growth potential.
  • Seek candidates aligned with long-term company success, not just immediate earnings.

What are key considerations when onboarding new sales reps?

Effective onboarding focuses on desired outcomes and early indicators of success.

\"...think about the key outcomes that you're looking for the seller to achieve... one of the first key outcomes is learning how to prioritize their book of business.\"

Takeaway:
  • Define clear initial outcomes for new sales reps.
  • Focus on leading indicators, not just final results.
  • Help reps prioritize their accounts effectively from the start.

How can startups improve their sales process by focusing on mindset?

Shifting from activity-based to mindset-based sales stages enhances sales effectiveness.

\"...we actually think about the mindset in each of those stages... at stage 2, we call that the curious investigator... we expect our sellers to embody the mindset of a value articulator.\"

Takeaway:
  • Define sales stages by the mindset sellers should adopt.
  • Encourage behaviors that align with each stage's goals.
  • Enhance customer interactions by focusing on mindset over tasks.

How can startups leverage AI to enhance their sales efforts?

AI tools can significantly improve efficiency in sales workflows.

\"...we use Notion AI... Now we use Notion Research mode that aggregates information... and creates a polished briefing doc within seconds.\"

Takeaway:
  • Utilize AI to automate time-consuming tasks like briefing docs.
  • AI can aggregate data from multiple sources quickly.
  • Embrace AI tools to enhance productivity and customer interactions.

How can startups prevent deals from stalling due to single-threading?

Relying on a single contact can jeopardize important sales deals.

\"...the common mistake is that you're single threaded, you're with the wrong people, and you're not multi-threaded enough... I would argue it's not a real champion if they're not willing to introduce you to more people...\"

Takeaway:
  • Ensure you engage multiple stakeholders within target organizations.
  • Test your champion's influence by seeking introductions to others.
  • Build relationships across different levels to secure the deal.

Why is cold calling still effective in sales?

Cold calling remains a powerful yet underutilized tool in modern sales.

\"Cold calling is hard... When you cold call someone and you get a rejection, that hurts... So if you are putting yourself out there and cold calling... you have to try it.\"

Takeaway:
  • Cold calling can set you apart as competitors avoid it.
  • It offers a direct channel to potential customers.
  • Embracing cold calling can lead to unique sales opportunities.

When should startups start outbound sales efforts?

Outbound sales can be crucial even for startups with strong product-led growth.

\"I would say it's always earlier than you think... as you go up market, those customers do not buy without talking to a human... and you don't get in front of those people with a product led motion.\"

Takeaway:
  • Start outbound sales efforts sooner to reach enterprise customers.
  • Recognize that senior executives may not engage through PLG channels.
  • Build an outbound team to complement your PLG motion.

What type of sales reps should startups hire first?

When building an initial sales team, hiring the right type of reps is essential for startup growth.

\"...we call them the Renaissance reps, where they're generalists, they're adaptable, they're highly skilled and communicating and collaborating with the internal stakeholders... and that's where you learn the most.\"

Takeaway:
  • Hire generalist sales reps who can adapt and collaborate across teams.
  • Early sales hires should focus on learning and building the sales playbook.
  • Avoid hiring traditional \"coin-operated\" sales reps too early.

How should founders define their ideal customer profile (ICP) in a PLG startup?

Defining the ideal customer profile (ICP) is crucial for startups transitioning from product-led growth to enterprise sales.

\"It's figuring out who is your ideal customer profile, and I strongly believe it's the founder, because that's not going to guide your go to market strategy, it's also going to guide your product roadmap and where do you continue to lean in.\"

Takeaway:
  • Founders should personally engage in defining the ICP to align product and sales strategies.
  • Interview customers to understand their motivations and use cases.
  • Use firmographic data to identify high-value customer segments beyond product usage signals.